Piperazine → Methyl 6-piperazinonicotinate

HRID 1416928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1416928
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8](Br)=[N:9][CH:10]=1)=[O:4].[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[N:9][CH:10]=1)=[O:4]

Komponenten

4

Edukt 2

HCID 4837PiperazineHCID 13349623Methyl 6-bromopyridine-3-carboxylate

Produkt 1

HCID 14987928Methyl 6-piperazinonicotinateAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 2-bromopyridine-5-carboxylic acid methyl ester (1.40 g, 6.5 mmol) and piperazine (5.59 g, 65 mmol) was dissolved in acetonitrile (50 ml) and heated at reflux temperature for 2.5 h. The reaction mixture was concentrated in vacuo, dissolved in dichloromethane (50 ml) and extracted with water (3×50 ml). The organic solution was dried (MgSO4) and evaporated in vacuo, affording 0.80 g (56%) of 2-(1-piperazinyl)-5-pyridinecarboxylic acid methyl ester.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux temperature for 2.5 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutiondissolved in dichloromethane (50 ml)
  5. extractionextracted with water (3×50 ml)
  6. dry with materialThe organic solution was dried (MgSO4)
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cc5dc57475d1403c848b26f31c936b05
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05916889

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